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Methods of forming alpha, beta-unsaturated acids and esters

Active Publication Date: 2006-01-31
BATTELLE MEMORIAL INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]The present invention can be particularly advantageous since it allows utilization of a continuous system for production of alpha, beta unsaturated acids and esters.

Problems solved by technology

Many of these methods can be expensive, time consuming and / or inefficient.
Additionally, for methods that utilize an expensive reagent such as anhydrides, regeneration of the reagent, although possible, is difficult and may be cost prohibitive.

Method used

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  • Methods of forming alpha, beta-unsaturated acids and esters
  • Methods of forming alpha, beta-unsaturated acids and esters
  • Methods of forming alpha, beta-unsaturated acids and esters

Examples

Experimental program
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Effect test

example 1

Batch Production of Alpha-Acyloxy Products

[0041]Anhydrous methyl lactate (1 ml) was combined with glacial acetic acid (15 ml) in a reaction vessel to form a solution. Concentrated sulfuric acid (0.1 ml) was added and the resulting solution was heated to a reflux temperature of about 73° C. at a pressure of 150 mm Hg. The resulting condensate was dripped into a soxlet containing SiO2 (disposed between the reaction vessel and a reflux condenser) to remove water from the vapor and recycle dried acetic acid back into the reaction vessel. After one hour, the reaction was terminated by cooling the solution to room temperature and venting the vessel to atmospheric pressure. Nuclear magnetic resonance (NMR) analysis of the solution indicated a product ratio of 2-acetoxy propionic acid to its methyl ester (methyl 2-acetoxy propionate) of about 1:1. Methyl acetate was also formed as a byproduct. The combined acid and methyl ester product yield was approximately 95% of theoretical (estimated b...

example 2

Production of Alpha-Acyloxy Products Utilizing Continuous Flow Simulation

[0044]In a distillation reactor at atmospheric pressure, an acid solution formed by combining 30 ml of glacial acetic acid with 0.5 ml concentrated sulfuric acid was maintained at approximately 114° C. A reactant solution was prepared by combining 5.0 ml of an 85% lactic acid solution, by weight (15% water) with 20 ml of glacial acetic acid, and was added dropwise to the distillation reactor. The resulting distillate was collected and analyzed by NMR. After 1 hour, the 2-acetoxy propionic acid product yield was greater than about 90%. A small amount of dimer or polymer was also detected.

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Abstract

The invention includes a method of forming an alpha, beta-unsaturated compound. A carboxylic acid is mixed with an alpha-hydroxy acid or an alpha-hydroxy ester and is esterified to form an alpha-acyloxy derivative. The alpha-acyloxy derivative is transformed into an alpha, beta-unsaturated derivative. The invention additionally includes a process of forming an acrylate. Lactic acid or a lactic acid ester is reacted with a first portion of acetic acid in the presence of a first catalyst to produce the corresponding 2-acetoxy propionic acid or ester. A non-reacted portion of the acetic acid is recycled. The 2-acetoxy propionic acid or ester is transferred to a second vessel containing a second catalyst, and acetic acid is liberated from the 2-acetoxy propionic acid or ester to produce a corresponding acrylic acid or acrylate ester. The acid or ester is subsequently esterified by reaction with an alcohol to form a desired acrylate ester.

Description

TECHNICAL FIELD[0001]The invention pertains to methods of derivatizing an alpha-hydroxy group, and methods of forming alpha, beta-unsaturated compounds.BACKGROUND OF THE INVENTION[0002]Various alpha, beta-unsaturated acids and esters are commercially valuable. Compounds such as acrylic acid and acrylates are used extensively for production of a variety of polymer materials, plastics and super-absorbants.[0003]A number of synthesis methods are currently utilized to produce alpha, beta-unsaturated compounds such as acrylic acid and its ester derivatives. Many of these methods can be expensive, time consuming and / or inefficient. Additionally, for methods that utilize an expensive reagent such as anhydrides, regeneration of the reagent, although possible, is difficult and may be cost prohibitive.[0004]It is desirable to develop alternative methods to generate alpha, beta-unsaturated acids and esters.SUMMARY OF THE INVENTION[0005]In one aspect the invention pertains to a method of formin...

Claims

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Application Information

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IPC IPC(8): C07C69/66C07B35/00C07C67/30C07C51/377C07C67/08C07C67/317
CPCC07C51/377C07C67/08C07C67/327C07C57/04C07C69/67C07C69/003C07C69/54C07C69/14Y02P20/10Y02P20/582
Inventor LILGA, MICHAEL A.WERPY, TODD A.HOLLADAY, JOHNATHAN E.
Owner BATTELLE MEMORIAL INST
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